Inspiration for the song came from Reed's observation of the Warhol clique; according to Reed, the song is "a very apt description of certain people at the Factory at the time. ... I watched Andy. I watched Andy watching everybody. I would hear people say the most astonishing things, the craziest things, the funniest things, the saddest things."[2] In a 2006 interview Reed's bandmate John Cale stated: "The song was about a girl called Darryl, a beautiful petite blonde with three kids, two of whom were taken away from her."[3] The song was Andy Warhol's favorite by The Velvet Underground.[4]

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The song was recorded at Scepter Studios in Manhattan during April 1966. It features a piano motif played by Cale (initially written as an exercise) based largely on tone clusters. The repetitive keyboard part was inspired by the style of his friend Terry Riley, with whom Cale had played in LaMonte Young's mid 1960s group in New York City. It was one of the first pop songs to make use of prepared piano[5] (a chain of paper clips were intertwined with the piano strings to change their sounds). The song also features the ostrich guitar tuning by Reed, by which all of the guitar strings were tuned to D.[4] Drummer Maureen Tucker plays tambourine and bass drum while guitarist Sterling Morrison plays bass, a chore that he hated, despite his ability on the instrument.[6]

Nico provides lead vocals. The song was originally recorded with only one track of her vocals; they were later double-tracked for the final album version. Most versions of the album use this version of the song, though the initial 1987 CD release uses the original mix without the double-tracking.

An edited version of the song was released in July 1966 as a single with "I'll Be Your Mirror" as a B-side. The song cuts out about half of the studio version at just under three minutes. It did not chart.

^Hoffman, Eric. "Examinations: An Examination of John Cale". Mental Contagion. Retrieved 24 October 2014. When I had to play viola, Sterling had to play bass, which he hated. According to the website, the quote is from John Cale’s autobiography, What’s Welsh for Zen (NY: St. Martin’s Press (2000).

^David Fricke, liner notes for the Peel Slowly and See box set (Polydor, 1995)